Your company is your boyfriend. I don’t think I’ve ever had less of a personal life than in the past year since I started Kaleidoscope. I spend all day talking to people, speaking on the phone, and in meetings so by the end of the day, I’m so over-socialized that all I want to do is go home, take a bath, and read a book in peace. I’m trying to do a better job of making time for a personal life now that we’ve launched the company and things feel marginally more stable.
As a part of our series about entrepreneurs who transformed something they did for fun into a full-time career, I had the pleasure of interviewing Ana Rosenstein the founder and CEO of Kaleidoscope Labs. She attended Brown University, graduating with honors in Political Science in 2015, and graduated from Harvard Business School in 2019. After graduating from Brown, Ana worked as an investment associate at betaworks ventures, a venture capital firm in New York focusing on consumer technology companies primarily in the media, audio, social network, and frontier technology (AI, VR) spaces. She then interned at JANA Partners, an activist hedge fund in New York focusing on consumer retail publicly traded equities. In the summer following her first year at Harvard Business School, Ana worked as a summer associate at RRE Ventures during which she developed the idea for Kaleidoscope and began building the company commuting between Boston and New York for an entire year to run the company and finish her second year at HBS simultaneously. Prior to joining betaworks Ana interned at The White House with the National Economic Council, CNBC with Maria Bartiromo’s Closing Bell, and Mashable.
Thank you so much for doing this with us! Can you tell us a bit about your “childhood backstory”?
I was born in New York but grew up between New York and San Francisco mostly because of my dad’s work. We commuted back and forth like crazy people, but I think because I never knew any different, I never found it jarring. My family moved back to New York full time when I started highschool. I left San Francisco kicking and screaming but in all honesty, have never looked back. From the time I was little, I was a ballerina and continued dancing all through high school, although I quit ballet my sophomore year due to injuries. I’m crazy about skiing. My whole family grew up skiing together but somehow I developed a real obsession with the sport. I actually spent two months skiing around the world alone before I started business school — it was the best two months of my life. I went everywhere — Riskgransen, Alyeska, Portillo, Valle Nevado, Verbier… the list goes on. I mention the dancing and the skiing because they were two important factors in my starting Kaleidoscope. As you can imagine, I’ve completely destroyed my body and live in a ton of pain. I obviously keep skiing nonetheless, despite the fact that my knee blows up to the size of a grapefruit when I do, but discovered a few years ago that CBD was tremendously helpful in curbing my pain.
But anyway, back to my backstory… I went to Brown for undergrad and studied political science with a focus in American politics. When I started at Brown I, embarrassingly enough, had a dream of being the first woman president… I quickly moved on from that aspiration but nevertheless remained fascinated by the American political process, particularly the history of the American presidency. In my senior year at Brown I was accepted into Harvard Business School’s 2+2 program. I worked in venture capital, at betaworks, for two years after college, and then left to get my MBA. I never dreamed I’d start a company. I thought I’d invest the rest of my life and stay on “that” side of the table. Starting Kaleidoscope is the most terrifying thing I’ve ever done with the steepest learning curve imaginable, but I absolutely love it…most of the time.
What was the catalyst from transforming your hobby or something you love into a business? Can you share the story of your “ah ha” moment with us?
I started Kaleidoscope by accident. In between my first and second years at Harvard Business School, I interned at RRE Ventures where I was tasked with devising a consumer retail/CPG investment strategy. About three weeks in, I had mostly been looking at health and wellness, and more specifically, CBD, and had this “ah-ha” moment. I came to the conclusion that the winner in the space hadn’t been built. I saw inconsistencies in the CBD ecosystem — why was an ingredient that was supposed to suppress anxiety and inflammation being put into sugary products like gummy bears or alcoholic beverages? Why would an ingredient with a notoriously low bio-availability (the amount of a substance that actually gets into the bloodstream) being put in food products where it would almost surely be broken down in the digestive system with only a small percentage actually reaching the bloodstream? I knew I wanted a scientifically crafted, premium CBD product that could be taken every day in a functional manner alongside all of my other vitamins and medications. CBD is functional, it’s not recreational and needs to be treated as such. All of these observations combined pointed me toward the concept for Kaleidoscope: a high-end CBD based capsule that could be incorporated into your daily routine but that targeted specific ailments and concerns thus giving customers control over the suite of products they ingest everyday.
There are no shortage of good ideas out there, but people seem to struggle in taking a good idea and translating it into an actual business. How did you overcome this challenge?
I started the company as a solo founder, which made turning the idea into reality incredibly daunting. I was commuting back and forth between HBS and New York twice a week trying to build a business while completing my MBA in a different state. Since I didn’t bring on any team members until about eight months into the journey, I had to develop a strategy that would make me feel a little less alone and a lot less helpless. So, I outsourced everything. Branding and manufacturing is routinely outsourced, but I went further. I outsourced accounting, marketing, advertising, supply chain, PR, and a host of other services I’m probably forgetting. Finding incredible partners — NSG/SWAT for marketing and advertising, FODA for branding, Anvyl for supply chain, Wells-Levitt for accounting… the list goes on — allowed me to finish up my MBA and build the company. Bringing on an amazing team obviously transformed the business. I brought on a COO from HBS, a chief of staff from my days at betaworks, and a bunch of other ambitious, creative people who allowed me to delegate, divide, and conquer to really get the business off the ground.
What advice would you give someone who has a hobby or pastime that they absolutely love but is reluctant to do it for a living?
Before you decide to do it for a living, you have to be really sure that your passion is in fact a viable business. The reason I say I started Kaleidoscope by accident is because I never wanted to start a company. I adamantly believed and still believe to this day that there are way too many startups being built and venture backed that shouldn’t be. If I hadn’t come up with an idea that a venture firm validated out of the gate, I don’t think I ever would have started a company. You have to be really sure that the thing you love can actually be a revenue generating business. If you don’t believe that’s the case, then it should remain a hobby you simply love doing in your spare time.
It’s said that the quickest way to take the fun out of doing something is to do it for a living. How do you keep from changing something you love into something you dread? How do you keep it fresh and enjoyable?
It’s rarely always fresh and enjoyable but even on the worst days, I can find a project or angle that gets me excited. I’m always coming up with creative ideas — whether that’s new product lines, crazy marketing strategies, new advertising channels, or planning events and pop-up stores. Those are the kinds of projects that in the middle of a day filled with paying bills and responding to customer service emails make me feel the way I did the first few weeks I started the company. There are always going to be parts of the job that you dread. No one likes paying bills or responding to hundreds of overdue emails. But the constant evolution of a new business keeps the days from becoming mundane or overly arduous.
What is it that you enjoy most about running your own business? What are the downsides of running your own business? Can you share what you did to overcome these drawbacks?
I love that I’m building a product everyday that I created out of necessity. The CBD product I wanted didn’t exist so I decided to bring it into the world myself. I love hearing from customers who love the product as much as I do and derive as much benefit as I hoped they would from Kaleidoscope. The biggest downside is that ultimately, the blame falls on me. Every bad decision, every failure, falls on my shoulders. Everyday goes from the lowest of lows to the highest of highs, back down, and then back up again. The missteps and failures along the way feel so much worse when I know I’m the one ultimately responsible.
Can you share what was the most striking difference between your actual job and how you thought the job would be?
Starting a company sounds glamorous. Even when you know the slim odds of success, you still conjure up this vision of crushing sales and blowing through all of your inventory on launch day. In reality, that stuff takes an insane amount of work and the smooth sailing that consumers see on the outside is far from smooth on the inside. You may think your fulfillment partner will seamlessly integrate with your website and send out every order perfectly but sometimes processes that seem like they’ll just “work,” in fact take a lot of manual labor and even more trial and error. Everything that looks perfect is in fact scotch taped and welded together. We do our best to make it look pretty but often the guts really aren’t.
Has there ever been a moment when you thought to yourself “I can’t take it anymore, I’m going to get a “real” job? If so how did you overcome it?
There isn’t a day that goes by that I don’t momentarily think, “I should give up and get a real job.” I don’t think there’s a concrete tactic to overcome that feeling. You just have to muster up the strength to keep charging ahead because, really, it’s the only option. There isn’t a magic bullet that gives you the strength to keep going. You keep going because you have to and you have to put on a brave face for the rest of your team.
Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?
When I started the company I had to use my home address as our mailing/business address. One of our investors has kindly let us squat in his office for free. While it’s amazing that we don’t pay rent, I had to use an alternate address for the business since our free offices were only temporary. An unforeseen consequence of using my home address for the business is that surprisingly often, packages (including large bulk shipments…) are sent to the billing address rather than the shipping address. Recently 20 boxes of product showed up at my apartment building. My doorman called in complete panic when hundreds of bottles CBD had overtaken his entire lobby.
Who has inspired or continues to inspire you to be a great leader? Why?
Corny answer, but, my dad. He’s my hero and my best friend. My dad has built an incredible career for himself from quite literally nothing. He’s smart, ambitious, and scrappy. He came from a crummy town in New Jersey and the thought of making it out seemed impossible. But he defied all odds. If I can do a fraction of what he has accomplished I’ll consider myself the luckiest girl in the world. He has set an example for me as an entrepreneur that pushes me further and harder everyday. He’s kind and compassionate but tough as hell. I can’t imagine any other leader I’d rather strive to emulate.
How have you used your success to make the world a better place?
I hope that our nonprofit, Kaleidoscope Gives Foundation, will ultimately make the world a better place. We care about organizations doing good in the cannabis sector and society as a whole. We’re adamant about criminal justice reform, we wholeheartedly believe there needs to be better research on the impact that cannabis can have as a medical substance, and we are in awe of the farmers striving to grow small businesses with sustainable environmental practices.
KGF provides grants to a variety of people and causes that are doing good on the cannabis industry. A percentage of sales from each bottle of Kaleidoscope product sold will go towards KGF, which then provides grant monies to fund various not-for-profit organizations and ventures doing exceptional things for the cannabis industry, the planet, and society.
What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)
- Your company is your boyfriend. I don’t think I’ve ever had less of a personal life than in the past year since I started Kaleidoscope. I spend all day talking to people, speaking on the phone, and in meetings so by the end of the day, I’m so over-socialized that all I want to do is go home, take a bath, and read a book in peace. I’m trying to do a better job of making time for a personal life now that we’ve launched the company and things feel marginally more stable.
- Always keep a “fancy” change of clothes in the office. I often come into the office in what I’ve been told is “meeting unacceptable attire.” I think the most egregious was when I showed up to the office in silk pajama pants, a knit poncho, socks with Birkenstocks, and a baseball hat. My chief of staff, Ale, looked and me and goes, “Ana, you must go home and change. You have a really important meeting in an hour.” At that point it was too late to run all the way back down to Nolita from midtown so we did our best to turn my outfit into some semblance of business casual. All that really consisted of was brushing my hair and removing the socks from under my Birkenstocks though.
- Get used to sink showers. Most of the time you’re going to be low on sleep, miss your alarm clock, and throw on the first things you see before running to the office. Sink showers are life savers in those moments. Always carry a toiletry kit with face wash, moisturizer, perfume, and sunscreen. Also, sink showers really suck when you’re working with an automatic, sensor sink. Trust me.
- The job is 90% meetings. I think if someone had told me that a year ago I would have chickened out. So maybe I’m glad no one told me. I’m famous for my “hatred of all people.” I say that in jest… But, honestly, I recharge alone and can easily get over-socialized and overstimulated. The back to back meetings all day are exhausting and my inbox definitely pays the price of never having time to sit at my desk and respond to the hundreds of unopened emails awaiting my reply.
- Driving sales is the biggest part of the job. When you start a company, the pre-launch/product development process feels like an insane amount of work. But, it’s nothing compared to the work that starts once you actually launch a product. Sales is the most important cog in the machine and it’s a really difficult and arduous process, particularly in the cannabis industry when so many of the traditional marketing channels aren’t available to us.
What person wouldn’t want to work doing something they absolutely love. You are an incredible inspiration to a great many people. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.
Gun control. It’s the most pressing issue in our country today. If there were sensible legislation such as mandatory background checks to purchase guns and restricting the carrying of firearms in certain locations, we could save so many lives. It’s an issue we can actually do something about. Reducing the number of gun deaths is actually something we could accomplish with the right legislation and a strong enough movement.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
“We are all worms, but I do believe that I am a glow-worm.” — Winston Churchill
For years I struggled with self confidence. I still often struggle with “imposter syndrome.” I have this constant feeling that somehow I’ve tricked everyone into getting where I am or that somehow I got here by accident. I love Churchill’s quote because it invokes the notion that we should all believe we’re glow worms. We’re still worms — slimy, dirt-dwelling creatures — but we can stand out in a sea of worms in our own way.
Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.
I have an unhealthy obsession with Stephen Colbert. Not only is he brilliant, witty, and political, but come on, he’s the sexiest man alive.
Thank you for these fantastic insights. We greatly appreciate the time you spent on this.
Phil La Duke is a popular speaker & writer with more than 400 works in print. He has contributed to Entrepreneur, Monster, Thrive Global and is published on all inhabited continents. His most recent book is Lone Gunman: Rewriting the Handbook On Workplace Violence Prevention listed as #16 on Pretty Progressive magazine’s list of 49 books that powerful women study in detail. Follow Phil on Twitter @philladuke or read his weekly blog www.philladuke.wordpress.com